Roof Flashing Repair in Connecticut.
Where 95% of Leaks Start.
Chimney, skylight, step, valley, and pipe boot flashing repair. NRCA-spec workmanship, no caulk-and-go shortcuts, 1-year leak warranty. statewide across all 8 CT counties.
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Licensed CT HIC.0703927 · Fully insured · No phone tag
Why flashing matters
Roof leaks are flashing leaks.
Walk into any NRCA technical conference and you'll hear the same number: roughly 95% of roof leaks originate at flashing details — chimney, skylight, valley, sidewall, pipe boot — not through the asphalt shingle field. The NRCA Roofing Manual dedicates a full volume to architectural metal flashing for a reason.
Asphalt shingles, properly nailed, do their job. Water hits the granule layer, runs down the laminated surface, and rolls off the eave. Flashings are different. They're the parts of the roof where two materials meet — metal and brick, metal and shingle, metal and stucco — and joints between dissimilar materials are where physics goes to break things over time. Thermal expansion is different for each material. Mortar shrinks; metal expands. Sealants UV-degrade. Fasteners back out.
None of this is new knowledge. It's why a roofer who understands flashing is the difference between a leak fixed once and a leak that comes back every spring.
What we repair
Six flashing details and how they fail.
Chimney apron + counterflashing
Two-piece system: base flashing nailed to deck under shingles, counterflashing tucked into a mortar joint above. Mortar joints crack over CT winters — that's usually where the leak starts.
Step flashing (sidewall)
L-shaped pieces of metal woven between each course of shingles where the roof meets a wall. Original installer often skips them or leaves gaps. Common leak source on dormers.
Skylight perimeter
Head, sill, and side flashings around the skylight. Sealant fails before glass does — 12–15 years is the typical window on a CT skylight.
Valley flashing
Metal in the valley where two roof planes meet. Open-valley assemblies have metal exposed; closed-valley assemblies have it under shingles. Debris dams and lifted shingles both compromise it.
Vent pipe boots
Rubber collars around plumbing stacks. UV-degraded rubber cracks at 8–12 years on a CT roof. Cheapest source of a leak.
Drip edge + kick-out
Drip edge at eaves and rakes redirects water away from the fascia. Kick-out flashing where a sidewall meets a roof edge is the single most commonly omitted detail on older CT homes — the leak shows up behind siding, not in the ceiling.
What we won't do
No caulk-and-go.
The fastest way to “repair” flashing is to smear roofing cement across the failure and walk away. We see it constantly. A previous roofer caulked over a counterflashing instead of repointing the chimney joint. The seal held for one or two CT winters, then cracked through, and the leak came back during the spring melt.
Manufacturer technical bulletins from GAF and Owens Corning are explicit: roofing cement is not a flashing material. It's a finishing detail at terminations. When we repair flashing, we replace the failed metal, re-set it into a fresh mortar joint or under the proper shingle course, and use sealant only where it belongs — as a secondary line of defense, never as the primary water barrier.
That's why the 1-year warranty doesn't scare us.
Flashing repair pricing
Published tiers. Written quote on arrival.
Trust Proof Roofing — published
$400–$600
Single flashing detail (pipe boot, step flashing section, vent collar).
$800–$1,300
Chimney counterflashing with mortar repointing, valley re-flash, skylight perimeter rebuild.
$300/hr + materials. $400 min ($500 if >50 mi from Hartford).
Written quote on arrival, before any work begins.
Flashing detail in progress
Brick colonial · CT crew on-site
Properly bedded shingles over flashing
What good flashing work looks like
Backed in writing
1-year leak warranty on flashing work.
If the area we re-flashed leaks again from our workmanship, we return free. In writing on every repair invoice.
Common questions
Flashing repair, answered.
Why does roof flashing fail so often?
Per NRCA, roughly 95% of all roof leaks come from flashing — not the shingle field. Flashings are made of metal (aluminum, copper, steel, lead) and they expand and contract with temperature far more than asphalt shingles. They're also where the roof plane gets interrupted by something taller — a chimney, a skylight, a wall. Every one of those interruptions is a place where two materials meet, and material joints fail before continuous surfaces do. Add 25 years of CT freeze-thaw cycles and you get the leak you're calling about.
What types of flashing do you repair?
Step flashing at sidewalls and dormers. Apron and back-pan flashing at chimneys. Counterflashing where the chimney mortar joint meets the cap. Skylight perimeter (head, sill, and side flashings). Valley metal where two roof planes meet. Plumbing vent pipe boots. Drip edge at eaves and rakes. Kick-out flashing at the bottom of a sidewall — often missed entirely on older CT roofs.
How do you know flashing is the source of my leak?
During diagnosis we work uphill from the interior stain — the water enters above and runs down. The first penetration uphill is the first suspect: a vent pipe, then a skylight, then a chimney, then a sidewall. We inspect each flashing detail visually and, if needed, do a hose test. About 19 leaks out of 20 are at a flashing.
How much does flashing repair cost in CT?
Most flashing repairs land in our small-tier range of $400–$600 — a single boot replacement, a step flashing detail re-bedded, or a chimney apron resealed. Chimney counterflashing repair with mortar repointing can move into the $800–$1,300 big-tier range. $300/hr plus materials is our published rate. $400 minimum, $500 if your home is more than 50 miles from Hartford.
Can you just caulk the flashing instead of replacing it?
Caulk is a finishing detail, not a repair. We see it constantly on second-opinion calls — a previous roofer slathered roofing cement across a failed counterflashing because it's faster than repointing the chimney joint. It buys six to eighteen months, then fails uglier. We don't do caulk-and-go. We replace or correctly re-set the failed flashing detail. The fix has to be mechanical, not cosmetic.
What kind of flashing material do you use?
Depends on the detail. Step flashings are typically aluminum or copper — we match what's on the rest of the roof. Chimney counterflashing is usually 16 oz copper or pre-finished aluminum, set into a fresh mortar joint. Vent pipe boots are EPDM rubber with an aluminum base for shingled roofs. Valley metal is 26-gauge galvanized steel or aluminum, 24" wide minimum per NRCA. Lead and copper last longest; aluminum is the price-performance pick and is what most CT homes have already.
Do you guarantee flashing repairs?
Yes. The same 1-year in-house leak warranty applies to flashing repairs as to any other repair work we do. If the area we sealed leaks again, we come back free.
Should I just have the whole roof replaced if the flashing is failing?
Only if the rest of the roof is also near end-of-life. Flashing details have shorter service lives than asphalt shingles — flashings often need replacement before shingles do. A flashing repair on a roof with 10+ years of shingle life left is a smart call. We'll tell you if we think otherwise.
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Get the flashing fixed once.
NRCA-spec details, photo-documented, 1-year leak warranty.